In this episode, we sit down with Ilan Sherr, VP of Investigations and Regulatory Response at Lineal, to explore how AI is reshaping legal work, investigations, and compliance.

Ilan shares how his background in competition law and regulatory enforcement led him to see early on that reactive approaches weren’t sustainable, pushing him toward building AI-driven methods to identify risk before it escalates. We unpack where organizations really stand on the shift to proactive monitoring, and why many teams are still relying on legacy eDiscovery practices that create inefficiencies and exposure. The conversation also digs into culture. While companies talk about proactive risk detection, those efforts often stall when transparency and accountability become uncomfortable. On the AI front, we tackle a growing question: when does not using AI become a defensibility issue? Ilan offers a practical view on how expectations are evolving and what legal teams should be thinking about now. Finally, we zoom out to strategy. Ilan explains what becomes possible when legal expertise is tightly integrated with data and technology, how that’s changing the role of investigations teams, and why, despite all the innovation, the hardest challenges are still human.

Ilan Sherr is Vice President of Investigations and Regulatory Response at Lineal, where he helps organizations deal with investigations and respond to complex regulatory scrutiny while advancing proactive, AI-enabled risk strategies. An award-winning legal innovator with over 20 years’ experience in competition law, regulatory enforcement, and global compliance, Ilan previously founded and led Aiscension, DLA Piper’s AI-driven risk-management business, recognized for transforming how organizations detect cartel and bribery risks. He has been named in The Lawyer’s Hot 100 and recognized by Legal Week, the Financial Times, and ALM for his work at the intersection of law and AI.

With Tax Day right around the corner, Laura and Kevin take a hard look at a question a lot of high earners quietly avoid: if you’re making great money in tech, why aren’t you actually on track to retire?

Haley Gray, CFP®, joins the pod to break down the gap between income and real wealth. She explains how strong salaries can create a false sense of security, especially when taxes, lifestyle creep, and equity compensation complicate the picture more than people expect. The conversation digs into how rapid income growth subtly reshapes spending habits, often locking people into a higher cost of living before they’ve built a solid financial foundation. Haley also unpacks the realities of equity comp, from RSUs to stock options, and why having too much tied up in one company can create risk that’s easy to overlook when things are going well. With a practical, no-nonsense approach, Haley walks through what “retirement readiness” actually means, how often people should be checking in on their progress, and the moment of truth many face when they finally run the numbers.

The big takeaway: making good money isn’t the same as building wealth. But with a few smart moves, starting now, it’s possible to get on track faster than most people think.

Haley Gray is a CFP® professional and Financial Advisor at Stellarix Group, where she works with professionals in technology and other fast-paced industries to navigate complex financial decisions with clarity and confidence. Her work focuses on retirement planning, tax strategy, and long-term wealth building, with an emphasis on areas that are especially relevant for tech professionals, such as equity compensation, variable income, and concentrated stock positions. Haley brings a modern, practical perspective to financial planning, helping clients simplify complexity and make smarter decisions with their money over time. She is known for her practical, education-first approach, helping clients focus on what actually matters and make confident financial decisions without unnecessary complexity. Her goal is to help clients build strong financial foundations that support both their careers and their long-term goals.

Haley Gray is a registered representative of and offers securities and investment advisory services through qualified MML Investors Services, LLC. Member SIPC. OSJ: 2000 S Colorado Blvd, Tower 2, Ste 800, Denver, CO, 80222-7952, (303) 692-8183. The Stellarix Group is not a subsidiary or affiliate of MML Investors Services, LLC or its affiliated companies. CA Insurance License #4087390

This week on That Tech Pod, healthcare cybersecurity gets a reality check. Ed Gaudet, Founder and CEO of Censinet, joins the show to unpack how he found his way into healthcare security and why it became the problem he chose to focus on long term. From there, the conversation moves quickly past surface-level explanations and into where things actually break inside health systems.

It’s not a lack of tools. It’s not a lack of awareness. Ed lays out how leadership gaps, misaligned incentives, and day-to-day operational pressures create the conditions for breaches, even in organizations that believe they’re in good shape. He also shares how he would test that assumption and what signals tell you whether a system is truly secure or just hoping it is. The episode digs into the tension between patient care and security, questioning whether it’s a real constraint or sometimes a convenient reason to avoid harder decisions. On the AI front, Ed separates what’s actually working from what’s getting too much credit, and highlights the parts of a breach that technology alone won’t fix. It wraps with a candid look at the hard truths the industry tends to avoid and what real accountability would look like if organizations took cybersecurity seriously.

Then stick around to the very end for a bonus poem that adds an unexpected close to the conversation.

Ed Gaudet is the Founder and CEO of Censinet, a company focused on healthcare cybersecurity and third-party risk management. With more than 25 years of software and technology leadership experience, Ed has held executive roles spanning product, marketing, and sales at companies including Imprivata, Liquid Machines, IONA Technologies, Rational Software, and SQA, Inc. At Imprivata, he served as CMO and later business unit GM, leading the creation of Imprivata Cortext, a cloud-based clinical communications platform recognized as best-in-KLAS. Ed holds multiple patents in mobile authentication, secure content sharing, and distributed data management, and he is a recognized speaker on leadership, healthcare, and regulatory compliance.